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Boston, MA, USA to Chicago, IL, USA from $40: 10 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Boston, United States of America
to
Chicago, United States of America

How to Get from Boston to Chicago: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$40 by trainBest price
1372 kmDistance
4h 22m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Boston to Chicago with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
Various
Plane
Average Duration
4h  22m
Estimated price
$89-632
Recommended
Company
Amtrak
Train
Average Duration
22h  22m
Estimated price
$40-300
Cheapest
route map
Distance: 1372 km
Duration: 4h 22m

See more options

Company
Various
Plane
Average Duration
4h  41m
Estimated price
$64-302
Company
Various
Plane
Train
Average Duration
6h  54m
Estimated price
$97-518
Company
Various
Train
Plane
Average Duration
5h  28m
Estimated price
$119-849
Company
Various
Train
Plane
Average Duration
6h  1m
Estimated price
$159-719
Company
Various
Bus
Plane
Average Duration
5h  17m
Estimated price
$168-439
Company
Self
Drive
Average Duration
16h  30m
Estimated price
$180-270
Company
Flixbus USA
Bus
Average Duration
22h  49m
Estimated price
$204-295
Company
Various
Bus
Plane
Average Duration
5h  33m
Estimated price
$228-519
Browse car rentalsExplore flights

Traveling From Boston to Chicago

Journeying from Boston to Chicago reveals a shift from the historic charm of New England to the vibrant, urban heartbeat of the Midwest, offering you a blend of rich history, diverse cultures, and stunning architecture.

Best Neighbourhoods in Chicago

Chicago's neighborhoods offer diverse experiences, each with its distinct flavor.

Wicker Park
• Known for vibrant arts and music scene.
• Unique boutiques and trendy eateries abound.
Lincoln Park
• Features expansive parks and gardens.
• Offers stunning views of Lake Michigan.
The Loop
• Heart of Chicago's business and commerce.
• Home to iconic architecture and theaters.

Best Times To Visit Chicago's Attractions

Timing your visits to Chicago's attractions can significantly enhance your experience.

Millennium Park
Early morning or weekdays are ideal to avoid large crowds.
The Art Institute of Chicago
Visit on Thursdays for extended hours and fewer visitors.
Navy Pier
Go during off-peak hours on weekdays to enjoy a quieter atmosphere.

Chicago Weather: What to Expect Year-Round

Chicago experiences a humid continental climate, with warm summers and cold winters, making spring and fall the best times to visit for comfortable temperatures. Weather can influence your travel plans, from the vibrant summer festivals to winter's festive activities, so being prepared is essential.

Dining Recommendation

Try the iconic Chicago deep-dish pizza, which features a buttery, thick crust layered with gooey cheese and a generous amount of toppings, offering a heartiness that's distinct from Boston's seafood-centric cuisine. The bustling pizzerias, often filled with laughter and local patrons, provide a lively atmosphere that sets your dining experience apart from the more understated charm found in Boston.

Boston - Chicago operators

Explore transport companies operating between Boston and Chicago, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Plane Show flights
Website
southwest.com

Plane from Boston (BOS) to Chicago Midway (MDW)

Average Duration
2h 47m
Estimated price
$110-260
Website
aa.com

Plane from Boston (BOS) to Chicago O'Hare (ORD)

Average Duration
3h 1m
Estimated price
$80-350
Website
delta.com

Plane from Boston (BOS) to Chicago Midway (MDW)

Average Duration
4h 35m
Estimated price
$150-470

Plane from Boston (BOS) to Chicago O'Hare (ORD)

Average Duration
3h 3m
Estimated price
$120-360
Website
united.com

Plane from Boston (BOS) to Chicago O'Hare (ORD)

Average Duration
3h 1m
Estimated price
$100-440
Train Show train routes
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from Boston to Chicago Union Station

Average Duration
22h 22m
Estimated price
$40-300
Bus Show bus routes
Contact phone
+1 214-849-8100
Website
greyhound.com

Bus from Boston to New York Midtown

Average Duration
4h 20m
Estimated price
$19-70
Contact phone
+1 (855) 626-8585
Website
flixbus.com

Bus from Boston to Boston Manchester Airport

Average Duration
1h 5m
Estimated price
$5-35

Bus from New York to Indianapolis, IN

Average Duration
11h 15m
Estimated price
$130-130
Website
palmlandlines.com

Bus from Indianapolis, IN to Chicago IL

Average Duration
3h 20m
Estimated price
$50-65

Boston to Chicago: Overview of Bus, Train, Flight, and Car Trips

Traveling between Boston and Chicago offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🚗 Embark on a scenic road trip from Boston to Chicago, spanning 995 miles of diverse landscapes and charming towns. The journey offers a perfect blend of urban excitement and natural beauty along the way. 💵 Travel budget-friendly with car rental prices ranging from $180 to $270 for the round trip from Boston to Chicago. Enjoy the flexibility and freedom of the open road while exploring iconic sights and hidden gems en route to the Windy City. 🏙️ Arrive in Chicago after approximately 16 hours and 30 minutes of driving, ready to dive into the vibrant culture, delicious cuisine, and architectural wonders that await in this iconic Midwestern metropolis. Prepare for an unforgettable adventure from the historic streets of Boston to the bustling cityscape of Chicago.
Average price
$180 - $270
🚂 Embark on a scenic train journey from Boston to Chicago with a direct service operated by Amtrak. The trip takes approximately 22 hours and 22 minutes, offering a comfortable and relaxing way to travel between these two vibrant cities. 🌆 Covering a distance of 1,190 miles, the train route presents an opportunity to enjoy picturesque views along the way. With prices ranging from $40 to $300, passengers can choose from various ticket options for their journey. Experience the charm of train travel while making memories from Boston to Chicago.
Departure Point
Boston station
Arrival Point
Chicago Union Station
Useful tips for train travellers
• Onboard services for your train trip from Boston to Chicago primarily include Amtrak’s dining car service. They offer a variety of meals, snacks, and beverages, including regional specialties. Depending on the time of day and duration of your journey, you may also find a cafe car that offers simple grab-and-go options. Be sure to check Amtrak’s menu online before your trip for current offerings.
• Amtrak provides several seating options on its Lake Shore Limited route, which operates between Boston and Chicago. The options include Roomette (sleeper), Family Bedroom, Deluxe Bedroom, Business Class seating, and Coach Class (Economy) seating. If you prefer a quieter experience, consider upgrading to Business Class for added amenities, including larger seats and complimentary beverages.
• For your trip from Boston to Chicago, two primary operators are Amtrak (amtrak.com) and the Lake Shore Limited route. If you’re traveling with Amtrak, you can visit their website for tickets and schedules. Additionally, once you arrive in Chicago at Union Station (chicagounionstation.com), you can leave your luggage at the Amtrak Baggage Service for a fee, and public restrooms are available.
🛫 Flying from Boston to Chicago is quick and convenient, with a direct flight taking only 2 hours and 45 minutes between Boston Airport and Chicago Midway Airport. 💸 Flight prices between Chicago and Boston can range from $89 to $632, depending on factors such as booking time, season, and seat availability. Planning ahead can help travelers secure the best deals for their journey.
Departure Point
Boston Airport
Arrival Point
Chicago Midway Airport
Useful tips for plane travellers
• Opt for Southwest Airlines or Delta, as they are the main carriers for direct flights from Boston to Chicago Midway; Southwest offers two free checked bags, which could save you money on your trip.
• Upon arrival at Chicago Midway Airport, follow the clearly marked signs for ground transportation; consider using the Midway Transit Center for easy access to buses and also be prepared for potential waiting times during peak hours.
• Taxi fare from Midway to downtown Chicago typically ranges between $30 and $40; for a more economical option, check the CTA train schedule for the Orange Line, which offers a quick & cost-effective ride into the city for about $2.50.
🚌 The journey from Boston to Chicago by bus involves multiple transfers and takes approximately 22 hours and 49 minutes. There is no direct bus service between the two cities. 🌆 Route options vary in duration and distance, with transfers in cities such as New York, Detroit, and Cleveland. Prices for the trip range from $204 to $295.
Departure Point
Boston station
Arrival Point
Chicago IL station
Useful tips for bus travellers
• Plan your transfers carefully; you'll need to switch buses in New York and Cleveland, so confirm the schedules in advance with Greyhound (greyhound.com) and OurBus (ourbus.com) to avoid long layovers.
• Be sure to bring snacks and entertainment for the long journey, as some legs can take upwards of 11 hours between transfers; consider packing a portable charger for your devices.
• Upon arrival at Chicago's Greyhound Station, familiarize yourself with the station map to locate key amenities like bathrooms, food vendors, and transportation options; also, check for local transit schedules, which can be found at transitchicago.com

Frequently asked questions

Find out more about the route from Boston to Chicago.

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The distance between Boston and Chicago is approximately 853 miles by air and 995.4 miles by road. Travel times vary depending on the mode of transportation chosen. The fastest option is by plane, taking around 4 hours and 7 minutes. Train travel takes 22 hours and 22 minutes, while driving by car takes approximately 16 hours and 30 minutes. Taking a bus is the longest option, with a travel time of 17 hours and 45 minutes.
The most cost-effective option for traveling from Boston to Chicago is by train, with prices ranging from $40-$300. Although it takes 22 hours and 22 minutes, it is a more affordable choice. However, if time efficiency is prioritized, flying is the quickest option, taking only 4 hours and 7 minutes, with prices ranging from $75-$500. Therefore, the choice between cost-effectiveness and time efficiency depends on individual preferences and priorities.
The prices for train tickets between Boston and Chicago can range from $40 to $300, depending on factors such as the time of booking and seat class. For bus travel between the two cities, prices can range from $14 to $147. These prices may vary based on factors such as departure time, bus company, and booking in advance. It is recommended to check with specific train and bus operators for the most up-to-date pricing information.
To travel from Boston to Chicago without using public transportation, you can opt to drive. The distance between the two cities is about 995 miles, and it takes around 16 hours and 30 minutes to drive from Boston to Chicago. Depending on factors such as gas prices and toll fees, the cost of the trip by car can vary between $180 and $270.
If you are looking to travel from Boston to Chicago without a car, your best options are by bus or by plane. Taking a bus is the more affordable choice, with prices ranging from $14 to $150 and an average travel time of 17 hours and 45 minutes. Flying is a quicker option, with a travel time of 4 hours and 7 minutes, but the cost can range from $75 to $500. Additionally, there is the option of taking a train, which costs between $40 and $300 and takes approximately 22 hours and 22 minutes.
Yes, there is a direct train link between Boston and Chicago. The Amtrak train service departs once daily from Boston and arrives at Chicago Union Station, with a journey time of approximately 22 hours and 22 minutes. However, there is no direct bus connection between Boston and Chicago. The OurBus service offers a route with transfers in Ithaca, NY, taking approximately 17 hours and 45 minutes.
The flight between Boston and Chicago typically takes around 2 hours and 30 minutes. However, the actual duration may vary depending on factors such as the airline, weather conditions, and flight traffic. As for the cost, prices for flights between the two cities can range from $79 to $501, depending on different factors like the airline, time of booking, and availability of seats. It is always recommended to compare prices and book in advance to secure the best deals.
There are numerous options for accommodations near Chicago. With over 1116 hotels available, travelers have a wide range of choices. Prices start at $58 per night, offering a variety of budget-friendly options. Visitors can choose from luxury hotels, boutique accommodations, and budget-friendly motels, ensuring there is something to suit every traveler's preferences and budget.

Trips to Chicago